Complexes of 2-acetyl-gamma-butyrolactone and 2-furancarbaldehyde thiosemicarbazones: antibacterial and antifungal activity.
Cobalt, nickel, copper and zinc coordination compounds of two thiosemicarbazones with general composition ML(2) (L: monodeprotonated ligand corresponding to 2-acetyl-gamma-butyrolactone thiosemicarbazone, HL(1), and 2-furancarbaldehyde thiosemicarbazone, HL(2)) and also complexes with general composition MCl(2)(HL(2)) were synthesized (except [NiCl(2)(HL(2))] and [Co(L(2))(2)]). The interaction of CuCl(2) with HL(2) gave [CuCl(HL(2))], a copper(I) complex. The ligands and metal complexes were characterized by IR, (1)H and (13)C NMR spectroscopy, and magnetic susceptibility measurements. The crystal structure of [Ni(L(2))(2)]x 2dmso was determined and a trans-square planar coordination of the two kappa(2)-N,S chelate rings forming polymeric strips through H-bonds with dmso was observed. Actually, in all the reported complexes both ligands behaved as kappa(2)-N,S chelates, except in the case of [Co(L(1))(2)] in which HL(1) is tridentate kappa(3)-N,S,O. The antimicrobial properties of all compounds were studied using a wide spectrum of bacterial and fungal strains. The copper complexes of HL(2) were the most active against all strains, including dermatophytes and phytopathogenic fungi. Most of the studied compounds, especially [Cu(L(1))(2)], presented good activity against Haemophilus influenzae, a very harmful bacterium to humans.
Rodríguez-Argüelles
María C
MC
Departamento de Química Inorgánica, Universidade de Vigo, Vigo, Spain.
Tourón-Touceda
Patricia
P
Cao
Roberto
R
García-Deibe
Ana M
AM
Pelagatti
Paolo
P
Pelizzi
Corrado
C
Zani
Franca
F
D015107:4-Butyrolactone / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D003035:Cobalt / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D018360:Crystallography, X-Ray; D005658:Fungi / Q000187:drug effects; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D009532:Nickel / Q000737:chemistry; D013882:Thiosemicarbazones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015032:Zinc / Q000737:chemistry
D000447:Aldehydes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D005663:Furans; D013882:Thiosemicarbazones; D003035:Cobalt; D003300:Copper; D009532:Nickel; D015032:Zinc; D015107:4-Butyrolactone; C060089:2-furoic acid